


Would It Have Mattered?

by FamilyTrucksterImagines (oncruisecontrol), oncruisecontrol



Series: Dean Winchester Reader-Insert One Shots [3]
Category: Supernatural
Genre: Arguing, F/M, Fluff, Light Angst, jealous!Dean
Language: English
Status: Completed
Published: 2017-08-21
Updated: 2017-08-21
Packaged: 2018-12-18 10:54:41
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,480
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11872875
Author URL: https://archiveofourown.org/users/oncruisecontrol/pseuds/FamilyTrucksterImagines, https://archiveofourown.org/users/oncruisecontrol/pseuds/oncruisecontrol
Summary: Dean helps you prepare for a date. Dean gives you a ride to the date. Dean watches your date. Dean gets chewed out.





	Would It Have Mattered?

“You know,” Dean said, leaning back on your bed as he watched you rifle through your closet, “you don’t seem awful excited about this date.”

You hummed softly. He wasn’t wrong. It’s not like you were dreading the coffee date, but it did give you approximately the same amount of adrenaline as a trip to the grocery store did. You had hoped no one would notice that, but it would be asking a lot to expect the guy you spent most of your time with to overlook your blank expressions and unwavering voice.

“It’s just not a big of a deal,” you muttered.

He gave the back of your head a confused look. “First date in what, five years, not a big deal?”

That sounded awfully embarrassing when he said it. Thing was, hunting didn’t exactly leave time or circumstance for dating. Hell, half of the people any of you showed interest in ended up evil or dead, and God knows you couldn’t date a civilian. Add to that the tall, model-attractive men who were always by your side, and your own intimidating prettiness, both of which made you entirely unapproachable. Dating just happened not to happen.

You chewed on your bottom lip but didn’t reply. Instead, you took out a hanger with the sleeveless black blouse with the lacy shoulders and shook it at Dean.

“No,” he said.

You finally turned around to blink at him. “What do you mean ‘no?’ You love this shirt on me.”

His lips pursed for a split second. “Too nice. You want understated.”

“Wow. You really sounded like a girlfriend there. Maybe when I get back, we can put on facemasks and overanalyze every word he said to me.”

Dean scowled. “I’m being a real good friend here. I don’t even think you should be going on this date and I’m still here helping you out.”

A soft smile pulled at your lips and you walked over to place a kiss on his cheek, causing him to beam up at you when you pulled away. “I kinda don’t have a choice. Garth set us up. It’d be awkward to refuse.”

Dean got up and took your place at the closet, apparently taking matters into his own hands. You plopped down onto the edge of the bed.

“Why’re you against it, anyway?”

He threw a grey V-neck at you and moved over to your dresser. “I got my reasons.” A pair of black jeans landed in your lap. “And the biker jacket.”

“It’s September.”

“It’s late September. It’s cold out. You could get sick.”

“Uh huh. Thanks, dad.” You looked up at him, tucking your feet under yourself. It was cute, watching him pick out your clothes for you like a teenage best friend would, albeit grumpily. “Now reasons, pal.”

He heaved a sigh. “For one thing, being _set up_? By _Garth_ , no less. That’s just…” He shook his head. “Plus, he’s a hunter. Hunters are all assholes.”

“Thank you.”

“Not you. I mean… a little bit you.” He wasn’t wrong. “And if you were meant to go on a date with someone, you’d be a bit happier about it. And above all that, I just… got a bad feeling about it. Don’t like it. Half tempted to force you to stay home.”

“Thirty-six, Dean. And not your sister.”

“I’m very aware that you’re not my sister, sweetheart.” You didn’t miss his way his eyes trailed down your body for a second.

“Cute.”

The man smirked. Throwing a glance at your clock, he sighed heavily. “Well if you insist on going on this thing, you should hurry up and get dressed. I’ll meet you at the Impala in ten.”

Your eyebrows came together. “Uh, why?”

“Because I’m driving you,” he answered, like it was the most obvious thing in the world.

“I’m sorry?”

“Have you replaced your truck’s tires yet?”

 “Well, no, but–”

“Burning daylight,” he said before stalking out.

You glared at the door as it swung shut, but finally pulled yourself up and put on the outfit he’d planned out for you (which you still found endlessly amusing.) As you touched up your makeup in the mirror, you felt a slight twinge of guilt. Even your makeup showed how uninterested you were: you’d gotten more gussied up to kill a ghoul.

It took almost as long to find your jacket as it did to otherwise get ready. Why was this place so huge and why did you constantly leave it draped over random furniture?

By the time you got to the garage, Dean was leaning against Baby and looking more impatient than you felt was deserved. He did open your door for you, though, which was sort of odd, but it was nice. He also chose your favorite cassette to play on the way there, but the drive was otherwise silent and his eyes stayed more focused on the road than you were used to.

You noticed just as much about him as he did about you. It was part of the teammate/unspoken best friend thing. Naturally, this meant that you caught on to his hot-and-cold-at-the-exact-same-time act. Of course, you knew that asking about it would do no good, him being Dean and all. You could already hear him saying ‘nothing’s wrong. I don’t know what you’re talking about.’

You chalked it up to his discomfort with the whole date thing and the already bad day he’d had and accepted the silence.

It was only broken when he parked across the street from the coffee house.

“Who gets coffee as a date?” he grumbled.

“People who spend all night killing things and will be on to the next town first thing in the morning.”

“Wouldn’t it be hard to go on a second date if he doesn’t live near you?”

“Probably.” You looked away from the café’s door, where you’d been staring, to meet his eyes. “I’m not too worried about it.”

He chuckled. “I always admire your pessimism, baby.”

Your eyebrows raised slightly, questioning the pet name. As though catching his own mistake, he averted his eyes back to the coffee shop.

“Is that… is that him?”

You followed his gaze to the man standing by the door, looking down at his phone. You nodded. Garth had sent you a picture of him while trying to convince you to give him a shot. It had actually been the thing to sway you; he was cute.

“No,” Dean said.

“No what?”

“No, you can’t go out with him.”

“And why not?”

“I know him. Me and Sammy hunted with him years ago.”

“So?”

“The guy’s a dick.”

“Scale of one to Gordon Walker.”

“Eight-point-five.”

You nodded slowly. “Okay.” You turned back to him. “I’ll call you if I need a ride back.”

“You’re going?”

“Eight-point-five ain’t gonna murder me in front of a café in broad daylight.”

Before he could protest further, you were out. Dean had been right about one thing: the jacket was a good idea. The eighty-five degrees it had been two days ago was down to sixty at most. You shoved your hands in your pockets as you crossed the street.

Your date gave you a cute smile as you approached and you thought that this might not end up that bad. No one ever said you weren’t shallow. He was nice enough; asked about your day so far and payed for your drink. You couldn’t give him too many details on your day – reading ancient Greek texts about gorgons wasn’t something you discussed when people were standing behind you in line. The same went for him, of course. Can’t talk about work. Fantastic.

The two of you decided to sit outside for privacy’s sake. As you stepped through the door, you noticed the black classic car parked across the street. It had been a good ten minutes since you climbed out of it. It should have been more than halfway home by now.

“What the hell?” you grumbled, narrowing your eyes at it.

“What was that?” the man you were with asked.

You shook your head. “Nothing. Sorry.” You gestured to one of the tables and ended up sitting facing the Impala. You could see Dean sitting there, arms crossed, staring straight ahead. _Jackass_.

Unfortunately, your date only asked you the one question the whole date. He spent the entire time telling you every damn thing about himself and making sure you knew how great of a hunter he was and the fact that he drove a motorcycle. (Where did he keep all of his gear?) Those things seemed to be the most important. He also threw in plenty of ‘people r dumb’ jokes. He seemed to get less and less handsome by the moment. Needless to say, you understood why he was rated at eight-point-five.

You tried not to let them, but your eyes kept wandering back to the Impala. Often, you found Dean unabashedly watching the two of you. You returned his gazes with glares, which unsurprisingly went unnoticed by the man in front of you.

When he finally ran out of coffee and self-centric conversational topics, you took the opportunity to tell him that you’d had a great time and if he’s ever in town, you should _totally_ get together, not meaning a word of it. You never wanted to sit through this again.

He vehemently agreed, which made you pray that he never returned to Kansas. He also offered to drive you back to the bunker, which you kindly refused.

You gave him a hug and watched him walk away, a fake smile plastered to your face. When you were sure he was out of sight, you let your mouth drop into an angry frowned and turned towards Dean. If looks could kill, he’d be a stiff by the time you got the door open.

He stared forward, refusing to make eye contact as you walked over.

The only thing that stopped you from ripping the passenger door off its hinges was how much he cared about the damn thing, though that should have been another reason for you to want to maim it.

“What the hell?” you half-yelled.

“What?”

“Why are you _here_?”

“I knew you’d need a ride.”

“He offered to drive me home.”

“And you said no.” He turned the key in the ignition and pealed into the street.

You opened your mouth, but chose not to respond. “Do you know how hard it was to focus with you watching me?”

He let out a humorless laugh. “If you liked him, you’d be able to focus. Let me guess. He was an asshole.”

You definitely weren’t going to respond to that one, either. “You know stalking someone during a date is a real dick move, right?”

He shrugged. Still didn’t look at you.

“Tell me why.”

“I told you I had a bad feeling about it.” He glanced at you. His voice was flat and cold. “Throw a fit tantrum all you want, but don’t act like I ruined your perfect date, alright? You weren’t enjoying it. I saw you. You wanted it to end five minutes after you sat down.”

“God, you sound like a jealous boyfriend.”

His jaw clenched, and he seemed to focus harder on the road.

And then it clicked; the grumpiness, his not wanting you to go, his not liking the guy, him opening the door for you, him playing your favorite music, him staying, _baby_. You sighed.

“You should have told me.”

He untensed a bit, like he was tired. “Would it have mattered?”

The fight melted away from you all at once, and your heart felt heavier from his words. “Yes, Dean. It would have.”

He ran a hand through his hair, and shook his head, but he didn’t say anything. After a while of waiting for him to respond, you turned back to the road. A few minutes passed by in silence, before you finally got fed up.

“Turn here.”

He hesitated, but did as you said. “Where are we going?”

“Trust me.” You continued to give him directions, which he followed wordlessly. When you found yourselves at a secluded, tree-shaded river bank you’d been to a hundred times on your own, you told him to pull over. Because he was still grumpy and needed everything spelled out for him, you also had to say “park” and “get out.”

He rested against the Impala’s hood, refusing to make eye contact with you as you stood beside him, hip leaning against the car with your arms crossed.

“I wouldn’t have gone out with him,” you said.

He glanced at you before looking back down at his feet. You got the feeling he didn’t believe you.

“I mean it. Why outsource the position of ‘jerk who wants to date me’ when I got one right down the hall?”

The corner of his mouth quirked up momentarily. You had a way of making him laugh even when you were fighting, and now he was holding one back.

“I’m sorry for throwing a fit, alright? I still think it was a dick move, but I get it.” You placed a hand on his arm. “You ever gonna look at me?”

With a deep breath, he relented, turning his head to you and letting his eyes meet yours. The progress was fantastic. Maybe one day he’d talk, too.

“You know, I’ve never been too fond of watching you with other girls, either. I, um, liked to tell myself that it was because I just didn’t like their personalities, but… it was definitely more the way you looked at them that bothered me.”

“You never said anything, either.”

“I was in denial, up until thirty seconds ago.” You looked down at your hand, where it rested on his arm. “Question is, were you?”

“No, not really.”

You nodded, looking back up at his green eyes, which were focused intently on you. “How long?”

“Uh,” he laughed, “long as I can remember.”

“You’ve been knowingly pining for me for years?”

“Don’t you dare laugh at me.”

“I’d never,” you lied.

He licked his bottom lip. “What happens now?”

“Well, now you kiss me, I think.”

He nodded and moved in front of you, lifting you up and sitting you on the hood of the car with him standing between your knees. “Yes, ma’am.” One of his hands reached up to cup the back of your neck while the other gripped the outside of your thigh, and then his lips were on yours. And God, did they feel good. Perfect. Soft and warm and well aware of what they were doing. When he pulled away, you found yourself trying to chase them.

“Are you still mad at me?” he asked, voice low and sexy.

Your gaze stayed glued to his lips. “You’ll make it up to me,” you mumbled.

**Author's Note:**

> (Find this story on Tumblr [here](https://cruisecontroller-imagines.tumblr.com/post/164461545101/would-it-have-mattered-dean-winchester-x-reader).)


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